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Water soluble thioglycosylated BODIPYs for mitochondria targeted cytotoxicity

Kesavan, Praseetha E and Pandey, Vijayalakshmi and Raza, Md Kausar and Mori, Shigeki and Gupta, Iti (2019) Water soluble thioglycosylated BODIPYs for mitochondria targeted cytotoxicity. In: BIOORGANIC CHEMISTRY, 91 .

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Official URL: https://dx.doi.org/10.1016/j.bioorg.2019.103139

Abstract

The facile synthesis of water-soluble mitochondria targeting thioglycosylated BODIPYs is reported. Thioglycosylated BODIPYs were synthesized in 25-26% yields via thioglycosylated dipyrromethanes in four steps. The dipyrromethanes and thioglycosylated BODIPYs were characterized by various techniques including HRMS, NMR spectroscopy and X-ray crystallography. In-vitro cellular investigations in skin keratinocyte (HaCaT) and cervical (HeLa) cancer cells revealed significant cytotoxicities with IC50 values between 23.83 to 48.61 mu M. The flow cytometry experiments revealed significant cellular uptake of thioglycosylated BODIPYs into HaCaT cells and thioglucosyl substituted BODIPY (9) showed higher cellular uptake and ROS generation than the rest of the molecules. The highlight of this study is the mitochondrial targeting by the neutral BODIPYs, as judged by the colocalization experiments using confocal microscopy.

Item Type: Journal Article
Additional Information: copyright for this article belongs to ACADEMIC PRESS INC ELSEVIER SCIENCE
Keywords: Thioglycosylated BODIPY; Fluorescence imaging; Mitochondria targeting; Water soluble BODIPYs
Department/Centre: Division of Chemical Sciences > Inorganic & Physical Chemistry
Depositing User: Id for Latest eprints
Date Deposited: 24 Oct 2019 11:38
Last Modified: 24 Oct 2019 11:38
URI: http://eprints.iisc.ac.in/id/eprint/63756

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